Sometime Friday morning, three men slipped behind some beds at Central Men's Jail in Santa Ana and disappeared into a hole in the wall.

They wriggled through the narrow tunnels of the maximum security jail's plumbing system, cutting through multiple layers of steel, metal and rebar, and emerged on the roof, where they rappelled down four stories with a makeshift rope and escaped.

Jonathan Tieu, 20, Bac Duong, 43, and Hossein Nayeri, 37, were discovered missing about 9 p.m. Friday when Orange County sheriff's jail personnel conducting a nightly head count came up three short. A search of the facility turned up a makeshift rope made from bedsheets and spare cloth, a rectangular hole cut in a steel screen behind some beds and a misplaced coil of razor wire on the roof.

The inmates, who were facing charges ranging from murder to kidnap and torture, were still at large Sunday and were presumed to be armed. Teams of investigators were searching locations in multiple counties, but there have been no confirmed sightings of the inmates. The FBI has offered a $20,000 reward for information leading to the men's capture, and the U.S. Marshals Service announced it is offering a $30,000 reward — or $10,000 for information leading to the apprehension of each fugitive.

Addressing reporters at a Sunday news conference in Santa Ana more than 40 hours after the inmates were discovered missing, authorities appealed to the public for help.

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"Investigators are now relying on information from the public as we are exhausting every lead we have," said Lt. Jeff Hallock of the Orange County Sheriff's Department.

The escape was the first jail break at the facility in downtown Santa Ana in nearly 30 years.

"This appears to be a very sophisticated operation," Sheriff Sandra Hutchens said.

Authorities are investigating the possibility that a fight that occurred about 8 p.m. Friday at the jail was staged deliberately to delay the head count to help hide the escape. The men bypassed three security checkpoints undetected. Authorities don't know where they got the tools to help in the escape or what they were.

Tieu is charged with murder, Duong with attempted murder and Nayeri with kidnapping and torture. They were among more than 384 inmates being held in connection with serious, violent crimes. All three men were housed in a large, dormitory-style cell with 65 other men.

"If they were considered an escape risk before this, they would not have been housed in a 68-man tank. I can guarantee you that," said Carrie Braun, spokesperson for the Orange County Sheriff's Department.

The Central Men's Jail, built in 1968, is a hulking concrete compound in Santa Ana's civic center with sheer walls and crowned with coils of barbed wire. The jail houses more than 900 inmates.

It's an older jail with a linear layout that Hutchens and jail experts say makes it harder to secure and guard. Because the cells are lined up in rows, deputies can't monitor what's happening in each cell at all times. Newer jails have a more circular layout that allows guards to see what's going on in each cell at all times. Linear jails also allow inmates to circulate through more parts of the facility on a daily basis, possibly allowing for coordination and planning.

"If you have someone in a cell block, you can't leave them locked down 24 hours a day," Hutchens said. "Unfortunately the reality is we will have escapes."

Law enforcement experts say county jails such as Santa Ana's weren't designed to hold large volumes of violent offenders and don't always have the resources to house them. The ratio of jail personnel to inmates at the Orange County facility is about 1 to 33, authorities said.

Escapes are a matter of "desire, resources and the time," said Chuck Jackson, a former Los Angeles County sheriff's chief who led the county's Correctional Services Department. Escapes take high levels of coordination and planning, but he's seen inmates breach jails with minimal equipment, such as a mini hacksaw smuggled inside the spine of a Bible.

Orange County sheriff's investigators are still trying to figure out exactly how the inmates managed to plan and execute their escape undetected.

Authorities believe the escape was planned for weeks, even months, and occurred Friday morning. Video surveillance appears to show a figure shining a flashlight beam on the jail's roof around that time, sheriff's officials said. Investigators are still reviewing the rest of the security footage to determine which way the men went. There's no indication that any man has left the country.

The men were last seen wearing orange jumpsuits, and it's not clear whether they had help once they breached the jail's walls.

Nayeri had been held without bond since September 2014 on charges of kidnapping, torture, aggravated mayhem and burglary. Nayeri and three other men are accused of kidnapping a California marijuana dispensary owner in 2012.

They drove the dispensary owner to a desert spot where they believed he had hidden money and then severed his penis, authorities said.

After the crime, Nayeri fled the U.S. to his native Iran, where he remained for several months. He was arrested in Prague, Czech Republic, in November 2014 while changing flights from Iran to Spain to visit family.

Duong was being held without bond since last month on charges including attempted murder, assault with a deadly weapon, shooting at an inhabited dwelling and being an ex-felon in possession of a firearm. His criminal history also includes multiple convictions for possessing and selling methamphetamine and avoiding arrest and burglary.

Tieu had been held in lieu of $1 million bond since October 2013 on charges of murder, attempted murder and shooting at an inhabited dwelling. His case is believed to be gang-related.

Authorities asked anyone with information to call the hotline at (714) 628-7085 or to call 911 with any sightings of the men.